Red Wing Wabasha Chukka

If you’re looking for something a little more classy to add to your collection, but also crave quality and durability, then a pair of shoes from Red Wing is a good look. This classic chukka boot features russet brown leather with a gum Vibram sole. Hand-sewn in the USA in Maine, this boot only gets better with age and comes at a bargain being almost $80 off retail.